


How Close is Close?

by Julibean19



Category: Teen Wolf (TV)
Genre: Aftercare, Anal Fingering, Anal Sex, BDSM, Baby Boy Stiles, Crying Stiles, Daddy Jackson, Daddy Kink, Forced Orgasm, Future Fic, Humiliation, Little Space, M/M, Multiple Orgasms, Oral Sex, Overstimulation, Pet Names, Possessive Jackson, Praise Kink, Rimming, Spanking, Sugar Daddy, Under-negotiated Kink
Language: English
Status: Completed
Published: 2016-06-20
Updated: 2016-06-20
Packaged: 2018-07-15 10:48:28
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 8,694
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7219405
Author URL: https://archiveofourown.org/users/Julibean19/pseuds/Julibean19
Summary: <blockquote class="userstuff">
              <p>"What happened with you and Derek?” Jackson asked, licking the foam from his upper lip.</p><p>“What makes you think anything happened?” Stiles shot back, taking a big gulp of his drink to avoid elaborating.</p><p>“I just found you in a BDSM club in San Diego when last I checked you were happily shacked up with a very possessive deputy sheriff werewolf, nowhere near here?”</p><p>... In which Jackson finds lost baby boy Stiles and insists he deserves the best Daddy in the world.  Which is of course, Jackson Whittemore.</p>
            </blockquote>





	How Close is Close?

**Author's Note:**

  * For [sassyshanks](https://archiveofourown.org/gifts?recipient=sassyshanks).



> Thanks to [sassyshanks](http://sassyshanks.tumblr.com) for the great Glompfest prompt: "babyboy Stiles Stilinski had a perfect relationship with Derek, no kinks, very vanilla, and then Derek left. Now Stiles is very broken and needs a daddy to take care of him wink wink"
> 
> This was my first foray into this kink and this pairing, so I hope I did alright. Thanks to all the amazing people of the TW fandom for inspiring and participating in cool fests like this!
> 
> Special thanks to [captainvonchan](http://archiveofourown.org/users/captainvonchan/pseuds/captainvonchan) for her tireless Beta work and [denaceleste](http://denaceleste.tumblr.com) for their epic cheerleadering!

“You look lost,” a familiar voice said into his ear, calling loudly over the house music that was blaring through the club.  

Stiles paused for a second before turning around, letting the face that matched the voice lock into his mind.  “And you’re _not_ lost, Whittemore?” he asked, inclining his head slightly to the right, and realizing that Jackson was further into his personal space than he had thought.  

“I’m not actually,” Jackson sneered, still hovering close to Stiles’ neck so he could speak softer, but directly into his ear.  “I’m a member here.”

“I wouldn’t have thought this was your style,” Stiles said, jutting his chin out toward the scene that was playing out in front of them.  A heavy set man dressed in leather pants and vest was flogging a slight, reedy woman who was tied to a St. Andrew’s cross.  A large crowd had formed around the podium.  Their interested murmurs built up to a dull hum that could be heard over the deep bass that was throbbing through the room.

“You’re right,” Jackson said, reaching for Stiles’ elbow and steering him into another corner.  “I don’t do girls anymore.”

“But the leather and flogging you do?”  Stiles asked as Jackson stopped them in front of another podium, this one much quieter, with two men, one on his knees, trussed up with fine rope, and the other standing over him, still fully dressed in jeans and a casual button-down.

“If that’s what my partner wants,” Jackson said smoothly, not going into detail.  “I’m a giver,” he said with air of seriousness that made Stiles stifle a giggle.  He didn’t want to interrupt the silver-haired Dom on the stage who was busy giving his sub instructions on exactly what he was going to do and when.

“Why do I find that hard to believe?” Stiles asked, still smiling slightly, eyes flicking up to Jackson’s and away from the scene in front of him.

“I don’t see why.  You know I’m a control freak, a perfectionist,” Jackson said, face open and honest.  “Took me a while to find out exactly how deep those desires ran, but it’s really not that surprising, is it?  I like for people to do what I want, when I want it, and I like rewarding those who comply willingly and with enthusiasm.”

“You kind of sound more like a mob boss than anything,” Stiles pointed out, turning his attention back to the sub on stage, who was now deftly opening his Dom’s jeans with his teeth and getting him out of his underwear.

“Very funny, Stilinski,” Jackson said, the tone of his voice reminding Stiles of how much of a douche he had been as lacrosse captain.  “I’m more interested in putting them behind bars.  I’m an adoption attorney now, you know, one of those white hat types.”

“Oh please,” Stiles said, rolling his eyes, “white hat or not, you can’t tell me you actually like children now.”

“No,” Jackson said, crossing his arms defensively, “not particularly.  But I like putting abusive assholes in jail.  People who prey on kids are disgusting.”

“Make a lot of money defending the innocent, do you?” Stiles asked, honestly curious why Jackson wouldn’t be working for a bank or hedge fund.

“I’m already rich, Stilinski,” Jackson told him, voice a little softer than before, “I have other interests, you know.”

“Right, like flogging naughty subs, huh?”

“I don’t know why you’re so caught up on the pain part of the equation, but for your information… it’s harder than it looks,” Jackson said, turning Stiles’ body back the way they came, so he could see the woman, still on the cross, back bright pink through her tan.  “You have to be really careful.  Push the limit, but never cross it.  Listen to your partner every step of the way, and that’s even more difficult when you have werewolf strength to contend with.”

“Have you ever hurt anyone?” Stiles asked, not sure he was interested in pain play at all, now that he saw it up close.  “Like actually hurt them?”

“No,” Jackson said, letting Stiles turn away, back toward the male couple, “I don’t tend to play those sorts of games when it’s my choice.  There’s much more to it than that.”

“It’s kind of hard to think in here,” Stiles said, feeling himself harden in his pants when the Dom finally came down his sub’s throat, and then got to his knees, kissing all over the younger man’s face and whispering sweetly into his ear until an exhausted smile spread across the sub’s face.  

The sub arched his back and sighed so happily when his Dom brought a calloused hand down to his lap and began to strip his cock, quickly, but precisely, keeping him right on the edge and then letting go, petting his hair and whispering in his ear again.  Then, abruptly, the younger man came, spurting with a jerk, his Dom’s hand nowhere near his cock, but still gently stroking the other man’s hair.

Stiles felt sweaty and dizzy just from watching them.  He brought a trembling hand up and wiped the moisture from his forehead, surreptitiously rubbing it on his thigh to dry it off.

“How about we go elsewhere for a drink?” Jackson suggested, cool fingers brushing across Stiles’ wrist as if to lead him away again.  “You look like you could use some air.”

“Don’t you want to stay?” Stiles asked, even as he followed Jackson toward the front of the club.  “I probably ruined your evening.”

“There’s nothing I need in there tonight,” Jackson said, holding the door open for Stiles, who felt the cool night air hit the sweat on the back of his neck.  “Trust me.”

They walked down the block to a pub, which was much more Stiles’ speed, and got a round of beers, settling into a booth.  Stiles looked Jackson over, wondering how he had got here.  He hadn’t seen the man in years, not since the wolf left Beacon Hills for Stanford, and he wondered how Jackson had even gotten himself settled without an Alpha.  Stiles never even thought to check on him, had just moved into an apartment with Derek near UC Davis while the rest of the pack went their separate ways.

“Do you have a pack here?” Stiles asked finally.  Seeing Jackson, completely cool and collected while his own life seemed to be falling apart had made Stiles curious.  Jackson’s life had been just as messy as anyone’s, with enough trauma and family issues to give even Derek a run for his money, and yet here he was, in a San Diego bar with Stiles, sipping on an IPA like he didn’t have a care in the world.

“Yeah,” Jackson said, glancing around at the other patrons to see how much privacy they really had.  “It’s pretty casual.  We go for runs on the full moons, but otherwise, we just keep to ourselves apart from occasional meetings.  I had to check with the Alpha before I moved here, but he didn’t have a problem accepting newcomers.  What happened with you and Derek?” Jackson asked, licking the foam from his upper lip.

“What makes you think anything happened?” Stiles shot back, taking a big gulp of his drink to avoid elaborating.

“I just found you in a BDSM club in San Diego when last I checked you were happily shacked up with a very possessive deputy sheriff werewolf, nowhere near here?” Jackson asked rhetorically, wondering how much Stiles might open up to him.  Derek had always been a very private person, but if things were over between them, Stiles might have a good rant bottled up inside.

“He left me,” Stiles said simply, looking down at the table, tracing the rings of condensation with his long fingers, dragging the water out like a starburst.

“Why?”

“I don’t know,” Stiles sighed, still not meeting his eye.  “Everything was perfect.  We were happy.”

“Nothing’s perfect,” Jackson said, tone soft and understanding, “you know what happened.”

“Everything was so vanilla, so sweet, so careful,” Stiles started speaking very quickly, letting the words tumble out.  “I just wanted something more, more passion, more crazy, and I pushed him.  I wanted him to let go, let his wolf out, but he refused, kept saying it was too dangerous, that he was giving me everything he could give.”

“Maybe he was,” Jackson offered, treading as lightly as possible.  “You know he had so much happen to him.  If he never worked through it all, I’m sure he couldn’t trust himself.  Maybe that _was_ all he could give you.”

“I think I triggered him,” Stiles admitted, shaking his head like he still couldn’t believe how stupid he had been.  “I was trying to get him to accept praise in bed.  I thought it might be good for him.  I called him a ‘good boy,’ and he snapped, ran out of the house.  When I got home from work the next day, he had packed up and left me a note… told me not to call.”

“Maybe it’s for the best,” Jackson said, laying his hand across the table in case Stiles wanted to take it.  He appreciated the gesture, but Stiles pulled his hands back into his lap instead of reaching out.  “If he really couldn’t give you what you needed.  You need to look out for yourself sometimes.  It’s not your job to hold everyone else together.  He has a lot of stuff to work through himself.  That’s not your fault.”

“I guess,” Stiles said, wondering when Jackson had become a sex therapist.  It must be all the work with traumatized kids that taught him how to comfort people.  “I just… between him and my dad, and Scott, I never really thought about myself.”

“You care,” Jackson said, taking his hand off the table to sip his beer, figuring the moment had passed.  “That’s not a weakness.  It’s not something that should be taken advantage of.  It’s something that should be given back.  You need someone to look out for you, too.”

“Maybe…” Stiles said, turning what Jackson had said over in his mind.  “I just feel like I could have done better.  I should have been happy with what we had.  It was good.  It was more than a lot of people get.”

“That’s not a reason to stay in a relationship that’s not working,” Jackson said.  Stiles let those words sink in.  It hadn’t been working.  That was true.  Maybe it wasn’t his fault.  They were just trying to force something that wasn’t meant to be.

“It shouldn’t have to be so hard,” Stiles said finally, looking up at Jackson’s clear blue eyes, silently thanking him for helping him to get to that conclusion.

“You’ll find someone new,” Jackson said, smiling with encouragement, “I know tons of people back at the club.  I can help you find what you’re looking for.”

“I don’t know what I’m looking for,” Stiles said honestly, taking a frustrated sip of his drink.  “I just want someone who cares as much as I do.  Someone who can take some of the pressure off me.  I’m sick of being the adult all the time, fixing things for everybody else.  I want someone to think about what I need for once.”

“Sounds like you need a Daddy,” Jackson said, lip curling up slightly at the corner, waiting for Stiles’ reaction.

“And what would that make me?” Stiles asked, a little worried at what the answer might be.  Disgusting?  Creepy?  Deviant?

“That makes you a baby boy,” Jackson said with a small smile, like he was letting Stiles in on some great secret.  Catching the fallen, pinched look on Stiles’ face, he added, “it’s nothing to be ashamed of.  You just have different wants and needs than other people.”

“Maybe I want something really different,” Stiles said, thinking back to what he saw in the club.  “I don’t want some burly, older dude trying to pound me into submission.  Why is there always a type?” Stiles speculated.  “With the leather and the body hair, and the—” he waved a hand in front of his entire person, gesturing to God knew what.

“I thought you were into the leather and body hair,” Jackson argued, smirking slightly.  “All evidence points to that being exactly your type.”

“Well maybe I need something new this time,” Stiles said, looking at Jackson over the top of his glass.  “Who says a Daddy can’t look like—” Stiles broke off, searching for a description of the image he had in his head..

“Like me?” Jackson asked, placing a finger on the rim of Stiles’ glass and pushing it lightly downward until Stiles put it back on the table, eyes still fixed on him.

“Wait— what?” Stiles asked, eyes flicking over every inch of Jackson he could see above the table.

“I’m not just into whips and paddles and leather,” Jackson said, trying his best to bring Stiles around to the idea.  “I know that’s not what you want.  You want to know how I know?”

“How?” Stiles asked dutifully, rolling his eyes at how Jackson was making him play along.

“I know you,” Jackson said simply.  “I’ve known you for years.  I’ve seen what you do, how you protect everyone, throw yourself into the line of fire without thinking about how much it might hurt, how it might kill you.  You put yourself last, every single time.”

“I do not—”

“You do,” Jackson said, firmer this time.  “You don’t even notice it, but you do.  With your father, Scott… the rest of the pack?  You need someone to put you first for once.”

“And you want to… do that?  With me?” Stiles asked, skeptical and confused.

“I think you deserve the best.  So yes,” Jackson said, self-satisfied smirk back on his face, “you deserve me.”

“Okay…” Stiles said slowly, draining his glass and putting it back down on the table with a clink.

“How much have you had to drink tonight?” Jackson asked, finishing his beer as well.

“Just this,” Stiles answered, picking up the empty glass and shaking it.

“Good,” Jackson said, standing up and straightening out his cuffs.  “Let’s go.”

“Okay,” Stiles answered easily, scrambling out of the booth and following quickly.  It hadn’t even occurred to him to ask why, or to make a date for another night.  Jackson asked him to leave, so he did.

They walked a few blocks until they reached a quiet neighborhood, beautiful old row homes lining the streets.  Jackson led him to the last one on the block, and opened the gate for him, waving him forward.

“Can you hear your neighbors through the wall?” Stiles asked, running his palm along the cool, marble countertop as he admired the modern kitchen.  He imagined that was why Jackson had chosen the house on the end of the street.  It only had one shared wall.

“Why?” Jackson asked, pulling two bottles of water from the fridge, “think you’re going to get loud?”

“It’s been known to happen,” Stiles said, marveling at his bravado, considering he had just decided he was going to do… whatever this was with Jackson.  It was like a game that he was never allowed to play before, the teasing, the tempting that he could do with Jackson that he could never do with Derek.

“I might have to learn to keep your mouth full then,” Jackson shot back, walking away, down the hall.  Stiles followed quickly, careening around the corner to keep Jackson in his line of sight.  He knew he must look pathetic, like an excited puppy, but he was too wound up to care.  This was the man who had been able to keep even perfect, demanding Lydia Martin happy for a while.  He was all too curious to find out what Jackson could do in bed.

He found the man in a beautifully furnished bedroom, black bed frame swathed in blue sheets that seemed to shine in the golden glow of the bedside lamp.  Jackson had put the two bottles of water on the nightstand and sat down on the edge of the bed, supported by his arms behind him, legs spread wide, almost like an invitation.

“Let me get a look at you,” Jackson said, looking down at the carpet between his legs, letting Stiles know he was meant to come closer.  Wiping his sweaty palms on his thighs, Stiles pulled his flannel straight and stood where Jackson indicated.  “Only you would wear flannel to a BDSM club,” Jackson said, “you looked so out of place.”

“Maybe I was just waiting for the right Daddy to find me,” Stiles suggested, freezing when Jackson ran a firm, strong hand across his waist and around to cup his hip.

“Is that what you’d like to call me?” Jackson asked, bright blue eyes cutting into Stiles like glass.

“If that’s okay,” Stiles said, wondering when that had become his goal and if he had already fucked everything up.

“If that’s what you’d like, but I won’t require it.  Sir is always appropriate,” Jackson said easily, looking Stiles up and down while he kneaded into his side over several layers of clothes.  “We haven’t gone through the whole negotiation process yet, so for now let’s just say that nothing you do tonight is wrong, and I'll always stop any time you ask me to.  If you have a question, ask it, you’re not getting in trouble tonight, alright?”

“Alright,” Stiles answered easily, wondering if he wouldn’t mind getting in a little bit of trouble if that meant he could see what Jackson’s control really looked like.

“Now, how about you show me what’s under all those layers?” Jackson asked, catching the corner of Stiles’ flannel between two fingers and gently pulling it away from his body.  Stiles licked his lips and pulled the offending garment off to reveal a tight, grey tee shirt.  He curled in on himself under the heat of Jackson’s gaze, holding one of his elbows with his other hand and shrugging his shoulders forward.

“You don’t need to be so shy, baby boy,” Jackson said, not a hint of sarcasm in his voice.   “You’re beautiful.  I’d be so happy if you would let me see you.”

Stiles blushed, feeling a little twitch in his pants at the pet name.  It already felt amazing, the attention Jackson was giving him, the careful choice of words.  He couldn’t remember the last time he felt like he had Derek’s undivided attention, and that’s what he was getting right now.  Jackson’s eyes never left him, he leaned back on his hands again, his stomach muscles flexing with every breath.  They seemed to come quicker and quicker the more Stiles took off.  He pulled the tee off over his head and lifted his gaze quickly to check Jackson’s expression before flipping open the button of his jeans.

“Can you come here, baby?” Jackson asked, standing up so they were on the same level once more.  Stiles moved into his space until they were almost pressed chest to chest, but Jackson pushed him back slightly, keeping him a foot or so away, which allowed him to run soft hands all the way up Stiles’ goose-bumped arms to his collarbone, and then up further to cup his face.

“You alright?” Jackson asked, and Stiles realized he hadn’t said anything for several minutes.  He let out a slow breath and nodded, letting Jackson rub his thumbs down the curve of his jaw and pull his chin up to look at him.

“It’s just intense,” Stiles said, finally finding his words.  “The way you look at me.”

“I’m looking at you like you’re the most important thing in the room,” Jackson said easily, leaning forward just as smoothly to press a full kiss to Stiles’ mouth, “because you are.”

“Thank you, Daddy,” Stiles said, ducking his head.  Jackson pulled his face back up and kissed him again, with an open mouth this time.  Stiles melted into him, pressing forward, happy to find that Jackson pulled him in, winding a hand into the back of his hair.  They stayed like that for a few minutes, kissing.  It was like what Stiles remembered kissing being when he was younger, like it was the main event, not just a brief stop on the expressway to sex.

When they pulled apart, Jackson still had a hand in his hair, kneading the back of his scalp.  Stiles nearly purred, it felt so good.  “Wow,” he said dumbly, realizing he had just had one of the best kisses of his life with his old lacrosse rival.  Jackson didn’t answer, just smirked and then attacked Stiles’ throat with a hot, tender mouth.  His tongue trailed up to Stiles’ ear, where teeth bit down sharply.  Stiles gasped, and let the hands on his hips turn him around until the back of his legs hit the bed and he was pushed down onto the plush mattress.

“Okay baby boy,” Jackson said, kneeling between Stiles’ open legs and reaching for his zipper.  “Let Daddy find out what his baby likes.”  

Stiles was speechless.  Jackson was still fully clothed, pulling Stiles’ jeans and briefs down at the same time, slipping his socks off his feet to leave a pile of somewhat sweaty clothes on the floor at the foot of the bed.  “Blue is my color,” Jackson said, running one hand down Stiles’ chest and one across the satin sheet beside him, “but you look better in red.  Maybe we’ll redecorate, huh?  Can’t have my baby looking less than his best, can I?”

Stiles nodded, licking his lips, unaware of the way his tongue was still hanging partially out of his mouth, resting against his bottom lip.  “Now I’m going to go over every inch of your milky white skin, and you’re going to make as much noise as you want, but you’re not going to come until I tell you, okay baby boy?”

“Yes, Daddy,” Stiles said immediately, feeling his eyes go wide as Jackson leaned down over his heavy erection and just breathed on it from an inch away.  Stiles hissed, his hips arching off the bed without his consent, trying to get closer to the wet heat of Jackson’s mouth.

“You stay where I put you, baby,” Jackson ground through his teeth, pressing Stiles’ hipbones back down to the bed with his palms.  “Baby boys listen to orders, or there are unfortunate consequences.”  Stiles nodded again, fighting to keep his body as still as possible when Jackson’s hands started running up his sides, stopping to rub at Stiles’ pert nipples with the pads of his thumbs.

His mouth followed, running in hot circles around Stiles’ nipple and then sucking, harder and harder until Stiles let out a gasp and began to squirm.  Jackson switched sides, and did the same thing, sliding fingertips down the crease of his of his thigh, just barely brushing over his balls.  Stiles hands tightened into fists at his sides when Jackson’s tongue left his nipple to trail down his chest, through his happy trail, and to the base of his dick.

“Daddy?” Stiles cried out, voice louder than he expected it to be in the quiet bedroom.

“Yes?” Jackson asked between licks, looking up from his perch between Stiles’ legs, mouth still obscenely open.  He looked unbelievable, and Stiles kicked himself for ruining the moment.

“Don’t you want to get undressed?” Stiles asked, sheepish, but determined.  He hadn’t gotten the chance to feel any part of Jackson apart from his mouth, which was incredible, but not enough.  He knew what Jackson looked like in high school, and now that he was in bed with the man, he wanted the full experience.

“Later,” Jackson said, leaning back down to take Stiles fully into his mouth.  He sucked for a few seconds, then drew back off.  “Right now I’m focused on you.  My baby boy has a perfect dick, and I haven’t gotten a proper taste yet.  Just try to relax, okay?”

“Yes, Daddy,” Stiles said, marveling at how easily the word rolled off his tongue.  He thought it was going to be weird.  He’d known Jackson since they were kids, and had never gotten along, always pushing each other’s buttons, but now, Jackson was different.  The way he spoke and moved, it was like he was settled, somewhere deep down inside.  It made something in Stiles squirm, eager to please, ready to have all that carefully wrought intensity focused on him.

Jackson spent several long minutes sucking and teasing the head of Stiles’ dick with his tongue.  Stiles started to whine, a high, broken sound when Jackson went deeper, drawing him down into the back of his throat with skilled precision.

He drew off saying, “That’s it little lamb.  That’s my baby’s sweet spot, huh?”

Stiles nodded again, licking his lips that had gotten dry from the way he was panting, mouth open in a silent scream as Jackson worked him over.

“Well then, how about you lift your legs up and show me your pretty place?” Jackson suggested, tapping Stiles’ ankle until he figured out what was being said and complied.  “There we go,” Jackson said when Stiles had hooked his hands behind his knees and brought them up toward his ears, exposing the pale skin of his ass.  “Look how perfect you are for me.  Thank you for showing me everything,” he said when Stiles began to blush, “you’re being so good for Daddy.  Can I taste you here, too?”

Stiles nodded again, red heat spreading down his cheeks to his chest, closing his eyes tightly when he saw how intently Jackson was staring at his hole.

“You remember I said you could talk, right little lamb?” Jackson said, and then leaned in, running his tongue over Stiles’ hole.

“Oh fuck, oh fuck, Jackson!” Stiles yelled when he felt a hot tongue breaching him.  Then “ouch, fuck!” a sharp pain hit him in the same place a moment later.

“What’s my name, baby?” Jackson asked, rubbing two fingers over Stiles’ wet pucker, waiting for his answer.

Knowing he would get smacked again if he answered wrong, Stiles paused for a second to make sure he had it right.

“Daddy?”

“Is that a question or an answer?” Jackson asked again, still rubbing where Stiles was most sensitive, distracting him.

“It’s an answer, Daddy,” he replied quickly, waiting to see what Jackson would do next.

“Good boy,” he said, eyes sparkling in the lamp light, before lowering his head once more and sucking at Stiles’ rim.  Stiles’ heart raced at the words, and then his breath caught when

Jackson’s tongue breached him again, slipping inside and lapping eagerly.

The torture went on for a few more blissful minutes with Stiles muttering, “oh fuck” at odd intervals until he felt a gentle tapping at his mouth.

“Open up, baby boy,” Jackson said, rubbing two fingers against his bottom lip until he allowed them into his mouth.  Stiles laved them with a slow tongue when his Daddy ordered him to, “get them good and wet, sweetheart,” wondering absently if they were the same two fingers that had slapped his hole in punishment just a few minutes before.

Once Jackson’s fingers were dripping wet with Stiles’ saliva, he brought them down to rub at Stiles’ entrance, pleased that his boy was following orders and still holding his knees up to frame his face.  “You’re so beautiful.  So perfect for me,” he crooned as he pushed in and brushed against Stiles’ prostate.

Stiles keened, arching his neck and giving Jackson a good view of his throbbing Adam’s apple.  He fought to keep his body against the bed as Jackson stretched him, strong fingers rubbing and tugging in a perfect rhythm.  Stiles rocked down into his hand, squeezing his eyes shut tight.

“Tell me how it feels,” Jackson ordered.  Stiles’ eyes snapped open at the words.  He didn’t say anything, just panted with his mouth open until Jackson prompted him again.  “I need you to tell me how it feels, baby boy.  Use your words.”

“I—I—”

“If you don’t answer me, I’ll stop.”

“No, don’t stop!” Stiles called back, sweat beading across his forehead.  “It feels so good, Daddy.  You’re rubbing me just right.  I’m close,” he panted.

“How close, baby boy?” Jackson asked, bringing his other hand up to form a tight ring around Stiles’ cock, just underneath the head.

“Can I—Can I come, Daddy?” Stiles gasped, rocking down hard onto Jackson’s fingers while his other hand tightened around Stiles’ shaft.

“I don’t know,” Jackson quipped, lip turning up at the corner into a smirk, “can you?”

“May I come?” Stiles asked, correcting the language.

“Ask me properly,” Jackson said, voice as firm as his hand that was now rapidly stroking Stiles.

“Please Daddy!  Please, may I come?” Stiles begged, breath catching in his throat as his body tensed in preparation.

“Come for me, little one.  Let me see you,” Jackson allowed.  “Eyes open!” he yelled, Stiles obeying him just in time to see his come shoot across his chest and up to his collar bone.  Jackson slipped out of his body and used gentle hands to lower Stiles’ legs, wiping up his come with a few fingers and bringing them to his own mouth.

Stiles just stared, dumbfounded, as Jackson pulled a small towel from his bedside table and patted the sweat from Stiles’ head and handed him a bottle of water.  “Sip slowly,” he prompted, eyes soft, skin crinkling in the corners.  “Was that okay?” he asked, wiping his hands with the towel and then tossing it aside.

“So completely okay,” Stiles babbled, sitting up to sip his water.  “It was incredible.”

“You up for more tonight?” he asked, tone even and without inflection, letting Stiles know either answer would be correct.

“Yes,” Stiles said, putting his bottle down on the table again and inching closer to Jackson.  Strong fingers going to his collar, Jackson stood from the bed and started undressing, eyes never leaving Stiles’.

“There’s lube over there,” Jackson said, head tilting toward the drawer.  “Knees and shoulders, baby, let me see how you can stretch yourself.”

Stiles complied readily, reaching behind himself with slippery fingers while he watched Jackson undo his pants out of the corner of his eye.  He worked himself up to three fingers, itching for a fourth, eager to show Jackson how much he could take.  The bed dipped as Jackson joined him.  Warm, dry palms massaged up his calves as Stiles arched and twisted, struggling to get the right angle.

“That’s enough, baby,” Jackson said, tugging lightly on his wrist.  “Hold yourself open for me.  Let me see that pretty place.”

Stiles adjusted his weight on his chest and used both of his palms to pull his cheeks apart, long fingers just shy of his hole.  He felt a flush rush down his face and across his chest when a hot exhalation of breath hit him where he was wet and open.  A shiver ran across his shoulder when Jackson’s hand ruffled his hair and then trailed down his spine to press on his lower back, making him widen his stance to stay upright.

“You ready for your Daddy, little lamb?” Jackson asked, rubbing a circle on Stiles’ back.

“Umm… Daddy?” Stiles asked, a little unsure of himself.

“Yes, sweetheart?”

“Can we do this so I can see you… and touch you, please?”

“Of course, baby,” Jackson said, “I’m sorry.  Your ass is just so amazing, I got distracted for a minute.  Roll over for me, alright?”

Stiles obliged, more than ready to get a good, long look at a fully nude Jackson.  The man in question laid down next to him, stretching out with his arms behind his head, the flex of his bicep drawing Stiles’ attention.  “You’re allowed to touch, little lamb,” he said, rolling to his side and propping his head up on one arm.

Licking his lips, Stiles trailed a finger through the divots of Jackson’s abs, letting out a little huff of laughter at the absurdity of it all.  He was here, with Jackson, who wanted to be his Daddy.  His unbelievably hot, generous, loving, _safe_ Daddy.  All he had to do was let him.  Stiles could do it.  He wanted to do it, just let go, let someone take care of him for once.  He could fall and let someone else catch him.  Someone who knew him, had watched him for years and knew what he needed.

Stiles leaned in for a kiss and… fell.

Jackson met him more than halfway, licking into his mouth and gripping his shoulder with a sense of ownership that Stiles wasn’t sure he had ever felt before.  This was his Daddy, and his Daddy owned him, entirely, and, Stiles dared to hope, irrevocably.  A hand slipped down his body to rest in the curve of his lower back, pressing him into his Daddy’s body, giving Stiles a good grasp of how large his erection was.

“I love the way you do that, baby boy,” Jackson said as soon as he pulled away, a satisfied, close-mouthed smile on his face.  “Been wanting to kiss those lips for years.  And that tongue… it’s so distracting.”

Stiles beamed at the praise.  A little fire lit in his chest when he thought about pleasing the man beside him.  Jackson cupped his face with one hand, making Stiles feel bold enough to reach down and grasp his Daddy’s erection, hot and hard, and wide enough that his fingers just closed around it.

“Do you want to ride Daddy’s cock, little lamb?” he asked, smiling when Stiles clambered to push him onto his back and straddle his hips.  “Easy, baby, easy,” Jackson murmured, reaching for the lube and pouring some onto himself while Stiles lifted up and waited, locking eyes on him until he nodded, giving Stiles permission to do what he had been aching to do since he followed his Daddy down the hallway an hour ago.

Stiles sank down in one smooth movement, pulling a curse from his Daddy’s lips.  He stifled a giggle, then planted his palms on his Daddy’s pecs and braced himself there so he could find his rhythm and bounce ecstatically in his Daddy’s lap.

“Slow down there, little one,” Daddy said softly, grabbing his hips with strong, sure hands and stopping the motion.  “I’m going to come in two minutes if you keep doing that.  Don’t you want Daddy to have a good time?”

“Yes, Daddy,” Stiles gasped, desperate to rock forward and have his Daddy’s thick cock rub at that spot deep inside his pretty place.  

“Then make it last, baby boy,” Daddy told him, smiling fondly at Stiles’ exertion, watching the red flush spread down his chest to color the rest of his body.  Sweat had darkened the color of Stiles’ hair so that it looked more black than brown, and he ran a hand through it without hesitation, reveling in the purr that escaped his boy’s throat.  “That’s it,” he encouraged, letting his other hand cup the small of Stiles’ back, “just like that.”

Stiles rocked down hard, his Daddy’s hand pushing him at just the right angle to make sparks shoot up his spine.  He groaned low and long, letting his head hang down as he sunk into the sensation.  Daddy pulled harshly on his hair, pulling his head back up.  

“Eyes on me, baby boy,” he ordered, voice stern.  Stiles’ eyes snapped up immediately as Daddy’s hips thrust upward, spearing him even deeper than he was before.  “Look how hard you are for me again,” Daddy said, nodding toward Stiles’ lap where his dick was standing tall.  “You’re so good, so hot and so tight, just for me.  Mine to fuck.  Mine to please.”

“Yes, Daddy,” Stiles whined, feeling his orgasm build.  The huge Daddy cock felt so perfect filling him up and stretching him wide.  But his Daddy wanted it to last, so he would make it last.  He was determined to be the best baby boy his Daddy had ever fucked.  Stiles wanted to be kept, to be cherished.  He just had to make it last like Daddy wanted, and he could be kept, he knew it.  

He couldn’t do it.  Daddy was pounding into him now.  Stiles’ hips could barely hold on, his hands gripped tight to Daddy’s chest so he wouldn’t be dislodged.  He had to be good, he had to, but it was too much.  

“Daddy, may I come?” he whined, eyes slipping closed, muscles bunched tight as he fought to stave off his orgasm.  “Please, Daddy.  I can’t hold it.”

“Just a few more minutes, baby boy.  This feels too good.  I need you to wait,” Daddy said, but it was no use.  With one more hard thrust, Stiles exploded, shooting come all over his Daddy’s chest and up even higher, a streak dripping off the point of his cleft chin.  

“I’m so sorry, Daddy,” Stiles cried, unable to keep the tears from leaking out of his eyes.  “I’m sorry, I didn’t mean to, I just—”

“It’s okay little lamb,” Daddy soothed him, wiping the tears off his baby’s cheeks with his thumbs.  “I told you wouldn’t get in trouble tonight, but I do want to punish you a little.  Is that alright?  We can wait until tomorrow when we’ve had time to talk.”

“No, Daddy,” Stiles moaned, eyes already lit up with excitement, even through the tears.  “Now is fine.  Anything you want.”

“Anything, baby?” he responded, lips quirking up at the corners as he spoke.  “I think you might regret saying that.”  Stiles just shook his head vigorously, letting his Daddy know he was serious, he would take whatever punishment he was due.  

“I wanted to be good for you, but I wasn’t—” Stiles said slowly, his voice breaking on the last word.  “I deserve a punishment.”

“Alright then, little lamb,” Daddy said, tone still soft as he thrust hard upward, reminding Stiles that he was still yet to be satisfied.  “This is your punishment.  I need you to come again for me.  Right now.”

Stiles hurried to comply, easing his right hand off his Daddy’s chest, happy that his nails couldn’t leave any marks on the wolf, and brought it down to his lap.  “Yes, Daddy,” he whispered, wiping the last of the tears off his face with his other palm. 

“No hands,” Daddy said, eyes hard and serious.  “You have to come just on Daddy’s cock.  Right now,” he warned Stiles again, cross and impatient.

Stiles nodded briskly, dropping his cock like he had been electrified and leaning back to put his hands on his Daddy’s knees instead so he wouldn’t be tempted.  He wanted to bounce ferociously, knowing he would need the speed to get himself off again, but his Daddy had already told him off for that earlier, and he didn’t want to disappoint him again.  Instead, Stiles gripped tightly to his Daddy’s knees and rolled his hips, arching his back tightly and grinding downward, determined to give his Daddy the ride of his life.  He had to make up for how he had disobeyed.  If it made Daddy happy, Stiles would never touch his cock again.

“That’s it, baby boy,” he crooned, meeting Stiles’ downward thrusts with his hips.  “Just like that.  Show me what those hips can do.  Make Daddy proud.”

Stiles panted, taking in shallow gasps of oxygen as often as he could, which was not nearly often enough.  He started to get light headed, sweat dripping down his back to pool where their bodies were joined, obscene squelching noises hitting his ears and making him blush even hotter than he already was.  He was exhausted, his body was sore, and he just couldn’t do it.

“I can’t—” he moaned, tears threatening to escape again.  “I can’t do it, Daddy—” Stiles cried, slumping, defeated into his Daddy’s chest.

“Oh yes you can, little lamb,” Daddy growled, planting his feet on the mattress and snapping his hips up sharply, over and over again, forcing Stiles to plant his hands on his muscular shoulders and dig his nails in.  “This is your punishment.  You asked for this… now you’re going to suffer through it like a good little boy.”

Stiles felt so worn out, barely able to keep his hands on his Daddy’s shoulders as he was fucked swift and deep.  Desperate to make his Daddy proud, Stiles tightened his overworked abdominals and slammed down onto his Daddy’s cock as hard as he could.  “Oh fuck, oh fuck, oh fuck,” he babbled, doing his best to squeeze his hole in little pulses, not wanting his Daddy to think he was too loose to be his baby boy anymore.  The movement served the dual purpose of bringing Stiles’ attention back to the way his pretty place was stretched wide by his Daddy’s cock.  Every stroke sent a little zing through his wrung-out body.  

“Harder, baby boy, harder!” Daddy called through the haze, Stiles’ eyes opening wide at the sound, “show me how you can come on your Daddy’s cock!  Show me right now!”

“I c-c-can’t—” Stiles stuttered, tears flowing freely now as his hole was wrecked by his Daddy’s thick cock.  “Please Daddy!” he whined, breath escaping him every time his Daddy pounded into his pretty place.  “I can’t unless you touch me!”

“Bad boys don’t get their little baby cocks touched,” Daddy told him, the words hitting Stiles like a death sentence.  “Bad boys have to wear plugs out to work with their Daddy’s come sloshing around in their bellies.  Bad boys have to put their little baby cocks in cages and wear clamps on their pretty pink nipples.  Bad boys don’t get help with their punishments.”

Stiles shuddered, hot shame and throbbing in his stomach at the thought of public punishment.  Daddy picked up on that right away.  He could tell by the stuttering in his baby’s hips that he had hit the right nerve.  

“You like that, huh?” Daddy asked, leaning forward until he was practically sitting up, abdominals flexing as he stretched up to lick the salty tears from Stiles’ face and talk soft and fast right into his ear.  “You want everyone to know you’re mine.  My perfect little fuck toy.”

Stiles gasped, not expecting his Daddy to use that kind of language, but clenching his body tighter all the same, even more wound up than he had been a minute ago.  

“I’m going to come in you so deep, I’ll be in you for days,” he muttered, hot and heavy against Stiles’ burning cheek.  “Then I’m going to plug you up and bring you to a pack meeting.  Let all those other wolves smell it on you, how creamy you are for your Daddy.  I’ll dress you up so nice and show everyone in the wolf den how pretty my little lamb is.  I’ll keep you plugged up for days, filling you up with load after load until you’re so full it’s just dripping out of you.  Every wolf in a hundred miles will know who you belong to.”

Groaning, Stiles felt his dick twitch with every shameful desire his Daddy expressed.  He was so close, sure that even the slightest brush would bring him off like his Daddy wanted, but he wasn’t allowed to touch.  Leaning back down, his Daddy spoke again.  Stiles struggled to hear what was said as the movement of the thick cock in his body held nearly all of his attention.

“Then I’m going to bring you back to Beacon Hills.  I’ll flaunt you all over town, let every ex-crush and nosy neighbor see how good you are for me, how perfect you are for your Daddy.”

Stiles shuddered, squeezing as hard as he could, desperate to get that very last bit of pressure that would send him over the edge, but he couldn’t.  His mind was focused on what Daddy wanted to do with him.  He had to hear the rest.

“I’m going to fuck you, baby boy.  All over town.  In the grocery store, at the library, in the hospital… I’m going to leave a trail of us everywhere we go.  Then I’m going to fuck you over a certain deputy sheriff’s patrol car.  Let him find us there, in broad daylight, let him hear how pretty you beg for your Daddy’s cock.  Show him a real wolf doesn’t need red eyes to own you.  Because you were never his.  Right baby boy?  He never deserved you.  You’re mine.  Say it.”

“Yours,” Stiles breathed, eyes rolling back in his head, casting his view toward the grey ceiling as he struggled to tumble over the edge for his Daddy.

“That’s right baby boy,” Daddy growled, voice going even lower.  “Mine to pamper and mine to punish.  So you’re going to squeeze that little pretty place tight around Daddy’s cock and come for me.  Just like I told you.  Right now.”

“I can’—” Stiles cried again, heartbroken that he couldn’t take his Daddy’s punishment.  No matter how fast his Daddy moved his hips, ramming right against his prostate, Stiles couldn’t come a third time.

“Yes,” Daddy ground out between his teeth as he brought a stiff hand down on his baby’s sweat-damp ass, “you,” he said, as another slap echoed sharply through the room, cutting through the high, broken-off pants coming from Stiles’ mouth, “can!” Daddy yelled, smacking down hard, leaving a bright red patch on the sensitive skin of Stiles’ inner thigh just as he jerked and spilled himself.  

Stiles broke apart.  His entire body tensed, lower abdominals aching with the strain as his cock exploded, lines of thin, watery fluid streaming across his Daddy’s chest.  With a heavy sigh, Stiles’ strings were cut.  He fell, loose-limbed onto his Daddy, not at all perturbed by the way his hot cheek rubbed against the sticky skin.  

“That’s it,” Daddy crooned, helping Stiles to slip off his softening dick and collapse fully across his body, long, mole-spotted limbs wrapping themselves around his neck as Stiles clung to him.  “It’s alright.  You did so good, baby boy.  You were perfect, perfect, perfect,” he whispered, rubbing soothing palms up and down Stiles’ back as he came down.  “I’m so proud of you.”

They stayed like that for long minutes, Jackson cradled Stiles against his chest until the heaving breaths stopped and he could no longer feel hot tears falling on his skin.  Ever so gently, Jackson raised his head, searching Stiles’ face for any sign of regret or prolonged discomfort.  Finding none, Jackson reached to the side table and found a towel, which he wet with his bottle of water and used to clean Stiles’ red, splotchy face.  “Here you go, baby,” he said, passing Stiles his half-full bottle and helping him tip it into his slack mouth.  “That’s good.”

Petting his hair, Jackson laid Stiles out on the bed, arranging his limbs in a comfortable position before going to the bathroom for a warm washcloth.  He cleaned Stiles’ face and chest, then moved lower to remove all evidence of Stiles’ multiple orgasms.  Rolling Stiles onto his side, he carefully wiped away the come and lube from his overused hole, checking the area thoroughly, then folded the towel over and cleaned the sweat from Stiles’ back.  After a quick swipe of his own body, Jackson laid down behind Stiles, tucking himself into the pronounced curve of his lower back.

“Jackson?” Stiles asked, soft but still present, reaching a hand out to grasp Jackson’s wrist and pull it tightly around his chest.  

“Yeah babe?” he replied, pressing a kiss to the side of Stiles’ pale throat, still a little salty and damp.  To Jackson, it tasted like a job well done, like a purge of every bad feeling Stiles had wrapped up inside himself.

“He left me.”

Jackson sucked in a deep breath and tucked his other arm under Stiles’ neck so he could press in tighter.  Letting the air out slowly, slightly ruffling Stiles’ hair with his exhale, Jackson muttered, “I know.”

“It wasn’t my fault,” Stiles said, tone flat and even.  

“No,” Jackson said, wanting to quash any doubts that might be creeping into the back of Stiles’ mind.  Just because he could say the words, it didn’t mean he would believe them immediately.  Jackson was sure it would take time and repetition to sink in.  “You did your best.  He couldn’t take care of himself, so he couldn’t take care of you.  It wasn’t your fault.”

“Promise?” Stiles asked, turning over in Jackson’s arms so he could see his face.

“Yes.  I promise,” Jackson said, letting Stiles search his eyes for affirmation.  Derek had broken the man in his bed.  Someone who had always put others first, always jumped into danger.  No matter how much shit he might have talked about letting people die, Stiles was the glue that held them together.  He deserved more.  He deserved better, and Jackson was more than happy to fix what Derek broke, no matter how long it took.  “How do you feel?” Jackson asked, wary of the fact that they hadn’t done much talking before they fell into bed together.

“Light,” Stiles answered, not even sure what he meant, but content in his response.  Stiles smiled, a joyful, bright thing that made Jackson’s usually reserved expression break into a reflection of Stiles’ contentment.  He actually laughed, Adam’s apple moving rapidly in his throat as he let the bubble of relief escape.

Jackson kissed him, slow and deep.  Cutting off the laugh and turning it into a moan, Stiles kissed back, letting Jackson’s tongue take over his mouth in an echo of their first kiss.  Stiles couldn’t believe it had only been a few hours since Jackson had found him in that club, nervous and downtrodden, unsure of what he expected to find.  He counted himself lucky that Jackson had been the one to take him home and put his pieces back together again.  

The kisses came slower, a few seconds in between each one where Jackson could just stare into Stiles’ honey brown eyes and take it all in, the desperation there.  Stiles had an eagerness to devote himself to something, someone, that shouldn’t be wasted.  Jackson kissed him again and then laid down on his back, easing Stiles’ head down to pillow on his shoulder.  He smiled knowingly.  Stiles had never belonged to someone before.  He had never been cherished by the likes of a Whittemore.  He had no idea what he was in for.  Jackson couldn’t wait.

“Get some sleep,” he said, pulling Stiles in closer, “we’re going shopping tomorrow.”

“Shopping for what?” Stiles asked, yawning, but nuzzling his face into the space between Jackson’s arm and chest, breathing in the comforting scent he found there.

“For you,” Jackson said, trailing a finger down Stiles’ bare arm, connecting the dots.

“I don’t need anything,” Stiles said, looking up with a questioning look, but then distracting himself with running the tip of his nose against the taut lines of Jackson’s throat.  

“Yes you do,” Jackson told him sternly, leaving no room for argument.  “You belong to me now… and I take care of what’s mine.  If you don’t let your Daddy take care of you, you’re going to need to be punished again.  Do you understand?”

“Yes, Daddy,” Stiles answered slowly, licking his lips and sucking a mark onto the curve of Jackson’s throat, pulling a groan out of the wolf that he decided to ignore in exchange for a good night’s sleep.  He could always worship his Daddy’s cock in the morning.  At that moment, the sheets were too soft to ignore.

“And I see that spanking might not be the best deterrent for you, so I’m going to have to get creative with your punishments,” Jackson warned, leaning over to shut off the bedside lamp.  With the room dark, Stiles pressed one last kiss to Jackson’s sharp cheekbone, and laid down for sleep.

  
“Yes, Daddy,” Stiles said again and closed his eyes, expecting nothing but pleasant dreams.

**Author's Note:**

> If you liked this, come [tumble](http://aflailureandamasterpiece.tumblr.com/) with me!


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